JPH0348643A - Production of non-cyclic ethyleneamines - Google Patents
Production of non-cyclic ethyleneaminesInfo
- Publication number
- JPH0348643A JPH0348643A JP18359089A JP18359089A JPH0348643A JP H0348643 A JPH0348643 A JP H0348643A JP 18359089 A JP18359089 A JP 18359089A JP 18359089 A JP18359089 A JP 18359089A JP H0348643 A JPH0348643 A JP H0348643A
- Authority
- JP
- Japan
- Prior art keywords
- monoethanolamine
- ammonia
- ethylenediamine
- phosphate
- phosphoric acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 125000004122 cyclic group Chemical group 0.000 title claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 50
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 42
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 21
- 239000000126 substance Substances 0.000 claims abstract description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000011574 phosphorus Substances 0.000 claims abstract description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 8
- 239000005977 Ethylene Substances 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 24
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 abstract description 6
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 5
- 229940005657 pyrophosphoric acid Drugs 0.000 abstract description 4
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- -1 acyclic ethylene amines Chemical class 0.000 description 11
- 238000000034 method Methods 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 5
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- 229960001124 trientine Drugs 0.000 description 4
- 229940048102 triphosphoric acid Drugs 0.000 description 4
- 125000002015 acyclic group Chemical group 0.000 description 3
- 235000011180 diphosphates Nutrition 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 229940048084 pyrophosphate Drugs 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052775 Thulium Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 2
- ZJXZSIYSNXKHEA-UHFFFAOYSA-L ethyl phosphate(2-) Chemical compound CCOP([O-])([O-])=O ZJXZSIYSNXKHEA-UHFFFAOYSA-L 0.000 description 2
- 229910052735 hafnium Inorganic materials 0.000 description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 229910001463 metal phosphate Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 229960004838 phosphoric acid Drugs 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000001226 triphosphate Substances 0.000 description 2
- 235000011178 triphosphate Nutrition 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- UFFAFBPZFGAMJJ-UHFFFAOYSA-N (2-methoxy-4,6-dimethylphenyl)boronic acid Chemical compound COC1=CC(C)=CC(C)=C1B(O)O UFFAFBPZFGAMJJ-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-O 1H-indol-1-ium Chemical compound C1=CC=C2[NH2+]C=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-O 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 101100145155 Escherichia phage lambda cIII gene Proteins 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 229910052689 Holmium Inorganic materials 0.000 description 1
- 229910052765 Lutetium Inorganic materials 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- JDRJCBXXDRYVJC-UHFFFAOYSA-N OP(O)O.N.N.N Chemical compound OP(O)O.N.N.N JDRJCBXXDRYVJC-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- IDCBOTIENDVCBQ-UHFFFAOYSA-N TEPP Chemical compound CCOP(=O)(OCC)OP(=O)(OCC)OCC IDCBOTIENDVCBQ-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- IOPOLWHQYJSKCT-UHFFFAOYSA-L barium(2+);dihydrogen phosphate Chemical compound [Ba+2].OP(O)([O-])=O.OP(O)([O-])=O IOPOLWHQYJSKCT-UHFFFAOYSA-L 0.000 description 1
- WAKZZMMCDILMEF-UHFFFAOYSA-H barium(2+);diphosphate Chemical compound [Ba+2].[Ba+2].[Ba+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O WAKZZMMCDILMEF-UHFFFAOYSA-H 0.000 description 1
- LYSTYSFIGYAXTG-UHFFFAOYSA-L barium(2+);hydrogen phosphate Chemical compound [Ba+2].OP([O-])([O-])=O LYSTYSFIGYAXTG-UHFFFAOYSA-L 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- XUYHBCPJXPJTCK-UHFFFAOYSA-L beryllium;hydron;phosphate Chemical compound [Be+2].OP([O-])([O-])=O XUYHBCPJXPJTCK-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CERDIVAFXRCORQ-UHFFFAOYSA-O butoxy-hydroxy-oxophosphanium Chemical compound CCCCO[P+](O)=O CERDIVAFXRCORQ-UHFFFAOYSA-O 0.000 description 1
- BNMJSBUIDQYHIN-UHFFFAOYSA-N butyl dihydrogen phosphate Chemical compound CCCCOP(O)(O)=O BNMJSBUIDQYHIN-UHFFFAOYSA-N 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-L calcium bis(dihydrogenphosphate) Chemical compound [Ca+2].OP(O)([O-])=O.OP(O)([O-])=O YYRMJZQKEFZXMX-UHFFFAOYSA-L 0.000 description 1
- 229940062672 calcium dihydrogen phosphate Drugs 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229960001714 calcium phosphate Drugs 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 1
- 235000019700 dicalcium phosphate Nutrition 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- MHJAJDCZWVHCPF-UHFFFAOYSA-L dimagnesium phosphate Chemical compound [Mg+2].OP([O-])([O-])=O MHJAJDCZWVHCPF-UHFFFAOYSA-L 0.000 description 1
- 229910000395 dimagnesium phosphate Inorganic materials 0.000 description 1
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 1
- QVKQJEWZVQFGIY-UHFFFAOYSA-N dipropyl hydrogen phosphate Chemical compound CCCOP(O)(=O)OCCC QVKQJEWZVQFGIY-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ZUNGGJHBMLMRFJ-UHFFFAOYSA-O ethoxy-hydroxy-oxophosphanium Chemical compound CCO[P+](O)=O ZUNGGJHBMLMRFJ-UHFFFAOYSA-O 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- XAKRTGZVYPZHCO-UHFFFAOYSA-O hydroxy-methoxy-oxophosphanium Chemical compound CO[P+](O)=O XAKRTGZVYPZHCO-UHFFFAOYSA-O 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 229910000157 magnesium phosphate Inorganic materials 0.000 description 1
- 229960002261 magnesium phosphate Drugs 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- QQFLQYOOQVLGTQ-UHFFFAOYSA-L magnesium;dihydrogen phosphate Chemical compound [Mg+2].OP(O)([O-])=O.OP(O)([O-])=O QQFLQYOOQVLGTQ-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 1
- 235000019691 monocalcium phosphate Nutrition 0.000 description 1
- 229910000401 monomagnesium phosphate Inorganic materials 0.000 description 1
- 235000019785 monomagnesium phosphate Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- MHZDONKZSXBOGL-UHFFFAOYSA-N propyl dihydrogen phosphate Chemical compound CCCOP(O)(O)=O MHZDONKZSXBOGL-UHFFFAOYSA-N 0.000 description 1
- PRAHMDIEZMWIRW-UHFFFAOYSA-N propyl dihydrogen phosphite Chemical compound CCCOP(O)O PRAHMDIEZMWIRW-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- AOKGFBICYSLGKE-UHFFFAOYSA-L strontium;dihydrogen phosphate Chemical compound [Sr+2].OP(O)([O-])=O.OP(O)([O-])=O AOKGFBICYSLGKE-UHFFFAOYSA-L 0.000 description 1
- HKSVWJWYDJQNEV-UHFFFAOYSA-L strontium;hydron;phosphate Chemical compound [Sr+2].OP([O-])([O-])=O HKSVWJWYDJQNEV-UHFFFAOYSA-L 0.000 description 1
- 150000003482 tantalum compounds Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 1
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
- JOPDZQBPOWAEHC-UHFFFAOYSA-H tristrontium;diphosphate Chemical compound [Sr+2].[Sr+2].[Sr+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O JOPDZQBPOWAEHC-UHFFFAOYSA-H 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野］
本発明は、アンモニア及びエチレンジアミンとモノエタ
ノールアミンとを反応させて、エチレンジアミン、ジエ
チレントリアミン、トリエチレンテトラミン等の非環状
のエチレンアミン類を製造する方法に関するものである
。[Detailed Description of the Invention] [Industrial Application Field] The present invention is a method for producing acyclic ethylene amines such as ethylene diamine, diethylene triamine, and triethylene tetramine by reacting ammonia and ethylene diamine with monoethanolamine. It is related to.
エチレンアミン類の工業的製造方法としては、１．２−
ジクロルエタンとアンモニアとの反応および水素添加触
媒の存在下、モノエタノールアミンとアンモニアとの反
応により製造されている（小野勲、化学経済、１９７９
年６月号、２０〜２７頁）。前者の方法では、エチレン
ジアミンの２倍モルに相当する多量の塩化ナトリウムが
副生し、しかも塩化ビニルモノマーも副生するため、廃
棄物処理に多くの処理費を必要とする。更に、塩素イオ
ンによる装置の腐蝕が著しいという欠点もある。また後
者の方法では、用途の少ない環状のアミンが２０％程度
も副生じ、用途の多い非環状のエチレンアミン類を製造
するには問題がある。As an industrial method for producing ethyleneamines, 1.2-
It is produced by the reaction of dichloroethane with ammonia and the reaction of monoethanolamine with ammonia in the presence of a hydrogenation catalyst (Isao Ono, Kagaku Keizai, 1979
June issue, pp. 20-27). In the former method, a large amount of sodium chloride equivalent to twice the mole of ethylenediamine is produced as a by-product, and vinyl chloride monomer is also produced as a by-product, so that a large amount of processing cost is required for waste treatment. Another drawback is that the equipment is severely corroded by chlorine ions. Furthermore, in the latter method, about 20% of cyclic amines, which have few uses, are produced as by-products, which poses a problem in producing acyclic ethylene amines, which have many uses.
本発明の課題は、アンモニアとモノエタノールとを原料
にする上記の方法の問題点、即ち、環状のアミンの副生
が多いという欠点を解決しうる方法を提供することにあ
る。An object of the present invention is to provide a method that can solve the problem of the above-mentioned method using ammonia and monoethanol as raw materials, that is, the drawback that a large amount of cyclic amine is produced as a by-product.
本発明者らは、このような実情を考慮し、アンモニア及
びエチレンジアミンとモノエタノールアミンとの反応を
鋭意検討したところ、特定の触媒および特定の反応方法
により極めて高い選択率で非環状のエチレンアミン類が
生成することを見出し、本発明を完成させるに至った。Taking these circumstances into consideration, the present inventors conducted extensive studies on the reaction of ammonia and ethylenediamine with monoethanolamine, and found that acyclic ethyleneamines can be produced with extremely high selectivity using a specific catalyst and a specific reaction method. The present invention was completed based on the discovery that the following is produced.
すなわち、本発明は、
アンモニア及びエチレンジアミンとモノエタノールアミ
ンならびにリン含有物質とを、リン酸もしくはその縮合
物を含有する触媒床に供給してアンモニア及びエチレン
ジアミンとモノエタノールアミンとを反応させることを
特徴とする非環状のエチレンアミン類の製造方法である
。That is, the present invention is characterized in that ammonia and ethylenediamine, monoethanolamine, and a phosphorus-containing substance are supplied to a catalyst bed containing phosphoric acid or a condensate thereof to cause ammonia and ethylenediamine to react with monoethanolamine. This is a method for producing acyclic ethyleneamines.
本発明の方法で使用するリン含有物質としては、リン酸
、亜リン酸、リン酸塩、亜リン酸塩、リン酸エステル、
亜リン酸エステル、ビロリン酸、三リン酸、ポリリン酸
、ピロリン酸塩、三リン酸塩、ピロリン酸エステル等が
ある。Phosphorus-containing substances used in the method of the invention include phosphoric acid, phosphorous acid, phosphates, phosphites, phosphate esters,
Examples include phosphite, birophosphoric acid, triphosphoric acid, polyphosphoric acid, pyrophosphate, triphosphate, and pyrophosphate.
リン酸塩、亜リン酸塩、ビロリン酸塩および三リン酸塩
としては、夫々のアンモニウム塩が好ましい。リン酸エ
ステル、亜リン酸エステルおよびピロリン酸エステルと
しては、夫々の酸と炭素数１ないし４のアルコールとの
エステルが好ましい。As phosphates, phosphites, birophosphates and triphosphates, the respective ammonium salts are preferred. As the phosphoric acid ester, phosphorous acid ester and pyrophosphoric acid ester, esters of the respective acids and alcohols having 1 to 4 carbon atoms are preferred.
例えば、リン酸エステルとしてはリン酸モノメチル、リ
ン酸ジメチル、リン酸トリメチル、リン酸モノエチル、
リン酸ジエチル、リン酸トリエチル、リン酸モノプロピ
ル、リン酸ジプロピル、リン酸トリプロピル、リン酸モ
ノブチル、リン酸ジブチル、リン酸トリブチル等がある
。亜リン酸エステルとしては亜リン酸モノメチル、亜リ
ン酸ジメチル、亜リン酸トリメチル、亜リン酸モノエチ
ル、亜リン酸ジエチル、亜リン酸トリエチル、亜リン酸
モノプロピル、亜リン酸ジプロピル、亜リン酸トリプロ
ピル、亜リン酸モノブチル、亜リン酸ジブチル、亜リン
酸トリブチル等がある。またピロリン酸エステルとして
はピロリン酸テトラエチル等がある。For example, phosphoric acid esters include monomethyl phosphate, dimethyl phosphate, trimethyl phosphate, monoethyl phosphate,
Examples include diethyl phosphate, triethyl phosphate, monopropyl phosphate, dipropyl phosphate, tripropyl phosphate, monobutyl phosphate, dibutyl phosphate, and tributyl phosphate. Phosphite esters include monomethyl phosphite, dimethyl phosphite, trimethyl phosphite, monoethyl phosphite, diethyl phosphite, triethyl phosphite, monopropyl phosphite, dipropyl phosphite, and phosphorous acid. Examples include tripropyl, monobutyl phosphite, dibutyl phosphite, and tributyl phosphite. Examples of pyrophosphate include tetraethyl pyrophosphate.
これ等のリン含有物質は単独でも２種以上の混合物とし
ても使用できる。特にリン酸、亜リン酸、ビロリン酸、
リン酸アンモニウム、亜リン酸アンモニウム、ビロリン
酸アンモニウム、リン酸モノエチル、リン酸ジエチル、
リン酸トリエチルが好ましい。These phosphorus-containing substances can be used alone or as a mixture of two or more. Especially phosphoric acid, phosphorous acid, birophosphoric acid,
Ammonium phosphate, ammonium phosphite, ammonium birophosphate, monoethyl phosphate, diethyl phosphate,
Triethyl phosphate is preferred.
これ等のリン含有物質の添加量は、モノエタノールアミ
ン１重量部に対してＰ換算でリン含有物質が１〜１００
００ ｐｐｍ（重量）、好ましくは１１０−１Ｏ００ｐ
ｐ （重量）である。＋ ｐｐｍより少ない量ではその
効果（活性の向上等）は少ない。一方１１００００ｐｐ
で十分な効果があり、通常はそれ以上の添加を必要とし
ない。The amount of these phosphorus-containing substances added is 1 to 100 phosphorus-containing substances in terms of P per 1 part by weight of monoethanolamine.
00 ppm (by weight), preferably 110-1000p
p (weight). If the amount is less than + ppm, the effect (improvement of activity, etc.) will be small. On the other hand, 110,000pp
is sufficiently effective and usually does not require further addition.
本発明で使用するリン酸もしくはその縮合物を含有する
触媒としては、リン酸、ピロリン酸、三リン酸等をシリ
カ、アルミナ、シリカ−アルミナ、珪藻土、粘土のよう
な（旦体に担持させたものや、リン酸、ピロリン酸、三
リン酸の金属塩がある。The catalyst containing phosphoric acid or its condensate used in the present invention includes phosphoric acid, pyrophosphoric acid, triphosphoric acid, etc. supported on silica, alumina, silica-alumina, diatomaceous earth, and clay. metal salts of phosphoric acid, pyrophosphoric acid, and triphosphoric acid.
リン酸の金属塩を例にして具体例を挙げると、リン酸二
水素ベリリウム、リン酸二水素マグネシウム、リン酸二
水素カルシウム、リン酸二水素ストロンチウム、リン酸
二水素バリウム、リン酸−水素へツリウム、リン酸−水
素マグネシウム、リン酸−水素カルシウム、リン酸−水
素ストロンチウム、リン酸−水素バリウム、リン酸ベリ
リウム、リン酸マグネシウム、リン酸カルシウム、リン
酸ストロンチウム、リン酸バリウムおよび周期律表３Ａ
族金属化合物とリン酸との反応物でＰ／金金属原子比１
〜６なる組成物、例えば、スカンジウム、インドリウム
、ランタン、セリウム、プラセオジム、ネオジム、サマ
リウム、ユーロピウム、ガドリニウム、テルビニウム、
ジスプロシウム、ホルミウム、エルビウム、ツリウム、
イッテルビウム、ルテチウムの水酸化物もしくは酸化物
とリン酸との反応生成物が挙げられる。Specific examples of metal salts of phosphoric acid include beryllium dihydrogen phosphate, magnesium dihydrogen phosphate, calcium dihydrogen phosphate, strontium dihydrogen phosphate, barium dihydrogen phosphate, and hydrogen phosphate. Thulium, magnesium hydrogen phosphate, calcium hydrogen phosphate, strontium hydrogen phosphate, barium hydrogen phosphate, beryllium phosphate, magnesium phosphate, calcium phosphate, strontium phosphate, barium phosphate and periodic table 3A
A reaction product of a group metal compound and phosphoric acid with a P/gold metal atomic ratio of 1
-6 compositions, such as scandium, indolium, lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbinium,
dysprosium, holmium, erbium, thulium,
Examples include reaction products of hydroxides or oxides of ytterbium or lutetium and phosphoric acid.
また周期律表４Ａ族金属化合物とリン酸との反応物でＰ
／金金属原子比１〜６なる組成物、例えば、チタン、ジ
ルコニウム、ハフニウムの水酸化物もしくは酸化物とリ
ン酸との反応生成物がある。In addition, P is a reaction product of a group 4A metal compound of the periodic table and phosphoric acid.
/gold metal atomic ratio of 1 to 6, for example, a reaction product of a hydroxide or oxide of titanium, zirconium, or hafnium and phosphoric acid.
具体的な化合物名として知られているものにリン酸−水
素チタン、リン酸−水素ジルコニウム、リン酸−水素ハ
フニウム等がある。Known specific compound names include titanium phosphate-hydrogen, zirconium phosphate-hydrogen, and hafnium phosphate-hydrogen.
また４価のバナジウム化合物とリン酸との反応生成物で
Ｐ／金金属原子比１〜６なるＩｌｌ成物、例えばリン酸
二水素バナジル（Ｐ／Ｖ ２）がある。There is also a reaction product of a tetravalent vanadium compound and phosphoric acid with a P/gold metal atomic ratio of 1 to 6, such as vanadyl dihydrogen phosphate (P/V 2).
また５価のニオブ、５価のタンタル化合物とリン酸との
反応生成物でＰ／金属原子比１〜６なる組成物がある。There are also compositions that are reaction products of pentavalent niobium or pentavalent tantalum compounds and phosphoric acid and have a P/metal atomic ratio of 1 to 6.
ビロリン酸と金属リン酸塩の項で例示した金属との塩お
よび、三リン酸と金属リン酸塩の項で例示した金属との
塩も使用される。Salts of birophosphoric acid with the metals exemplified in the section of metal phosphates and salts of triphosphoric acid with the metals exemplified in the section of metal phosphates are also used.
本発明の方法でアンモニア及びエチレンジアミンとモノ
エタノールアミンとを反応させるときには、通常アンモ
ニアとモノエタノールアミンのモル比を１以上に保持し
て反応させる。このアンモニアとモノエタノールアミン
のモル比を１未満に保持して反応させると、ピペラジン
、アミノエチルピペラジン等の環状物質が多量生成する
。好ましくはこのモル比を６〜５０の範囲に保持して反
応を行う、このモル比が大きくなる程環状物質の生成が
抑えられるが、生産能率は悪くなる。When ammonia and ethylenediamine are reacted with monoethanolamine in the method of the present invention, the molar ratio of ammonia and monoethanolamine is usually maintained at 1 or more. When the molar ratio of ammonia and monoethanolamine is maintained at less than 1 and the reaction is carried out, a large amount of cyclic substances such as piperazine and aminoethylpiperazine are produced. Preferably, the reaction is carried out while maintaining this molar ratio in the range of 6 to 50. The larger the molar ratio, the more suppressed the formation of cyclic substances, but the worse the production efficiency.
また通常、エチレンジアミンとモノエタノールアミンの
モル比を０．０１〜１０に保持して反応させる。Moreover, the molar ratio of ethylenediamine and monoethanolamine is usually maintained at 0.01 to 10 for the reaction.
このモル比が大きくなるにつれてアンモニアとモノエタ
ノールアミンとの反応で生成する正味のエチレンジアミ
ンの量が少なくなり、ジエチレントリアミン、トリエチ
レンテトラミン、テトラエチレンペンタミン等が多く生
成するようになる。好ましくはこのモル比を０．０５〜
５の範囲に保持して反応させる゛。As this molar ratio increases, the net amount of ethylenediamine produced by the reaction between ammonia and monoethanolamine decreases, and more diethylenetriamine, triethylenetetramine, tetraethylenepentamine, etc. are produced. Preferably this molar ratio is from 0.05 to
Keep it within the range of 5 and react.
反応温度は１５０〜４００ ’Ｃである。１５０“Ｃ未
満では反応速度が遅く、４００’Ｃを越えると生成した
エチレンアミン類の熱分解が大きくなる。好ましい反応
温度は２００〜３５０“Ｃである。The reaction temperature is 150-400'C. If it is less than 150"C, the reaction rate is slow, and if it exceeds 400"C, the thermal decomposition of the produced ethylene amines becomes large.The preferred reaction temperature is 200 to 350"C.
反応圧力は通常１〜１０００ｋｇ／ｃＩＩＩである。圧
力が高いほど非環状のエチレンアミン類の選択性が高く
なる。The reaction pressure is usually 1 to 1000 kg/cIII. The higher the pressure, the higher the selectivity for acyclic ethyleneamines.
本発明の方法では固定床方式を用いる。反応物の供給速
度は０．１〜３０、好ましくは０．２〜ｌＯｇ総反応物
／（ｇ触媒・ｈｒ）を採用する。また触媒はシリカ、ア
ルミナ、シリカ−アルミナ、珪藻土、粘土等のような物
質上に担持させることもできる。The method of the invention uses a fixed bed system. The feed rate of the reactants is from 0.1 to 30, preferably from 0.2 to lOg total reactants/(g catalyst·hr). The catalyst can also be supported on materials such as silica, alumina, silica-alumina, diatomaceous earth, clay, and the like.
リン酸とチタン化合物とから得られた反応生成物を触媒
に使用する際には、担体を使用して触媒の強度を強くす
ることが好ましく、担体としてはソリ力が適している。When using a reaction product obtained from phosphoric acid and a titanium compound as a catalyst, it is preferable to use a carrier to increase the strength of the catalyst, and a warping force is suitable as the carrier.
反応液からの生成物の分離は、例えば蒸留により容易に
実施できる。その際分離したアンモニア、エチレンジア
ミン、モノエタノールアミンは反応器に戻し、再使用す
ることができる。Separation of the product from the reaction solution can be easily carried out, for example, by distillation. Ammonia, ethylenediamine, and monoethanolamine separated at this time can be returned to the reactor and reused.
本発明の方法によりアンモニア及びエチレンジアミンと
モノエタノールアミンよりエチレンジアミン、ジエチレ
ントリアミン、トリエチレンテトラミン等の非環状のア
ミンを高収率で製造することが可能になる。The method of the present invention makes it possible to produce acyclic amines such as ethylenediamine, diethylenetriamine, and triethylenetetramine in high yield from ammonia, ethylenediamine, and monoethanolamine.
実施例１
肌
二酸化チタン３９．９５．に８５％リン酸１７２．９４
ｇを添加し混錬した。次いで微細なシリカゲル９７．
６１ｇ及び水１９０ｇを添加してｌｎｉ！！シ、押し出
し成型した（径３胴）。その後１５０’ｃで３時間乾燥
し、次いで５００°Ｃで５時間焼成した。このようにし
て製造した触媒を長さ３ｍｍに切断した。Example 1 Skin titanium dioxide 39.95. 85% phosphoric acid 172.94
g was added and kneaded. Next, fine silica gel97.
Add 61g and 190g of water and lni! ! Extrusion molded (3 cylinders in diameter). Thereafter, it was dried at 150°C for 3 hours, and then fired at 500°C for 5 hours. The catalyst thus produced was cut into 3 mm length pieces.
この触媒５４．８４ ｇを内径２５．８ｍｍのステンレ
ス鋼製の反応器に充填し、モノエタノールアミン１３．
５ｇ／ｈｒ、アンモニア５５．５ｇ／ｈｒの速度で供給
し、温度２８０ ’Ｃ１圧力４００ｋｇ／ｃｍＧの条件
テ４０００時間反応を行った。その後、反応；・夜を冷
却して反応を停止し、゛触媒を抜き出した。この抜き出
した触媒を使用し、次の実験を行った。この触媒は活性
が低下していた。54.84 g of this catalyst was charged into a stainless steel reactor with an inner diameter of 25.8 mm, and 13.8 g of monoethanolamine was charged.
5 g/hr and ammonia at 55.5 g/hr, and the reaction was carried out for 4000 hours under the conditions of temperature 280' C1 pressure 400 kg/cmG. Thereafter, the reaction was stopped by cooling overnight, and the catalyst was taken out. The following experiment was conducted using this extracted catalyst. This catalyst had decreased activity.
（反応開始前Ｐ／Ｔｉ ３．００ 、反応後Ｐ／Ｔｉ
１．５５）反応
内径１０＠ａ、長さ７６６ｍｌ１１の反応管に、前記の
活性の低下した触媒１０ｇを充填した。リン酸トリエチ
ルを７容解したモノエタノールアミン（リン酸トリエチ
ルをＰとして５００重ｆｆｉｐｐｍ含有している。）１
．９７ｇ／ｈｒ、エチレンジアミン２．５３ｇ／ｈｒ及
びアンモニア８．２６ｇ／ｈｒの速度で供給し、温度２
８０’Ｃ１圧力４００ｋｇ／ｅＪＧの条件で反応を行っ
た。結果を第１表に示した。(P/Ti 3.00 before reaction start, P/Ti after reaction
1.55) A reaction tube with an internal diameter of 10@a and a length of 766 ml was filled with 10 g of the catalyst with reduced activity. Monoethanolamine containing 7 ml of triethyl phosphate (contains 500 ffipm of triethyl phosphate as P) 1
．． 97 g/hr, ethylenediamine 2.53 g/hr and ammonia 8.26 g/hr, temperature 2
The reaction was carried out under the conditions of 80'C1 pressure and 400 kg/eJG. The results are shown in Table 1.
三成分とは、エチレンジアミン、ジエチレントリアミン
、トリエチレンテトラミンである。The three components are ethylenediamine, diethylenetriamine, and triethylenetetramine.
第１表に記載したように、アンモニアとモノエタノール
アミンとの反応に使用して活性の低下した触媒を使用し
、且つ、アンモニア及びエチレンジアミンとモノエタノ
ールアミンとの反応をリン含有物質（リン酸トリエチル
）を触媒床に供給しながら行うと、触媒活性及び触媒の
三成分への選択性が向上するのが観察される。すなわち
、触媒活性の低下した触媒（反応後の液にリン酸分が抽
出されてリン酸分が反応前よりも低下している。）や、
新しい触媒を固定床で使用して、アンモニア及びエチレ
ンジアミンとモノエタノールアミンとを反応させて非環
状のエチレンアミン類を製造するのに、触媒床にリン含
有物質を供給しつつ反応を行えば、触媒性能を向上させ
ることや、触媒のライフを長くすることが可能である。As described in Table 1, a catalyst with reduced activity is used for the reaction of ammonia and monoethanolamine, and a phosphorus-containing substance (triethyl phosphate) is used for the reaction of ammonia and ethylenediamine with monoethanolamine. ) is observed to be fed to the catalyst bed, an increase in catalyst activity and selectivity of the catalyst towards the three components is observed. In other words, a catalyst with reduced catalytic activity (the phosphoric acid content is extracted into the liquid after the reaction, and the phosphoric acid content is lower than before the reaction),
Using a new catalyst in a fixed bed, ammonia and ethylenediamine are reacted with monoethanolamine to produce acyclic ethylene amines. It is possible to improve the performance and extend the life of the catalyst.
三成分への選択率−Selectivity to three components −
Claims (1)
アミンならびにリン含有物質とを、リン酸もしくはその
縮合物を含有する触媒床に供給してアンモニア及びエチ
レンジアミンとモノエタノールアミンとを反応させるこ
とを特徴とする非環状のエチレンアミン類の製造方法。1 A non-cyclic ethylene product characterized in that ammonia and ethylenediamine, monoethanolamine, and a phosphorus-containing substance are fed to a catalyst bed containing phosphoric acid or a condensate thereof to cause ammonia and ethylenediamine to react with monoethanolamine. Method for producing amines.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18359089A JPH0348643A (en) | 1989-07-18 | 1989-07-18 | Production of non-cyclic ethyleneamines |
| US07/551,086 US5082972A (en) | 1989-07-17 | 1990-07-11 | Process for preparation of acyclic ethyleneamines |
| CA002020993A CA2020993A1 (en) | 1989-07-17 | 1990-07-12 | Process for preparation of acyclic ethyleneamines |
| EP90113520A EP0409116B1 (en) | 1989-07-17 | 1990-07-14 | Process for preparation of acyclic ethyleneamines |
| DE69012906T DE69012906T2 (en) | 1989-07-17 | 1990-07-14 | Process for the production of acyclic ethylene amines. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18359089A JPH0348643A (en) | 1989-07-18 | 1989-07-18 | Production of non-cyclic ethyleneamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0348643A true JPH0348643A (en) | 1991-03-01 |
Family
ID=16138482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18359089A Pending JPH0348643A (en) | 1989-07-17 | 1989-07-18 | Production of non-cyclic ethyleneamines |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0348643A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008101882A (en) * | 2006-10-20 | 2008-05-01 | Ube Ind Ltd | Solid fuel carrier pipe |
| JP2008101883A (en) * | 2006-10-20 | 2008-05-01 | Mitsubishi Heavy Ind Ltd | Burner for flame-retardant fuel |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6078945A (en) * | 1983-10-06 | 1985-05-04 | Mitsui Toatsu Chem Inc | Production of diethylenetriamine |
| JPS61236753A (en) * | 1985-04-15 | 1986-10-22 | Mitsui Toatsu Chem Inc | Production of diethylenetriamine |
| JPS62265251A (en) * | 1986-05-13 | 1987-11-18 | Tosoh Corp | Production of polyethylene polyamine |
-
1989
- 1989-07-18 JP JP18359089A patent/JPH0348643A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6078945A (en) * | 1983-10-06 | 1985-05-04 | Mitsui Toatsu Chem Inc | Production of diethylenetriamine |
| JPS61236753A (en) * | 1985-04-15 | 1986-10-22 | Mitsui Toatsu Chem Inc | Production of diethylenetriamine |
| JPS62265251A (en) * | 1986-05-13 | 1987-11-18 | Tosoh Corp | Production of polyethylene polyamine |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008101882A (en) * | 2006-10-20 | 2008-05-01 | Ube Ind Ltd | Solid fuel carrier pipe |
| JP2008101883A (en) * | 2006-10-20 | 2008-05-01 | Mitsubishi Heavy Ind Ltd | Burner for flame-retardant fuel |
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